Fluorescent dye N,N′-dioctadecylrhodamine as a new interfacial acid–base indicator

Mchedlov‐Petrossyan, Nikolay O.; Vodolazkaya, Natalya A.; Bezkrovnaya, O. N.; Yakubovskaya, A.; Tolmachev, A. V.; Grigorovich, A. V.

doi:10.1016/j.saa.2007.06.011

Cited by 17 publications

(22 citation statements)

References 20 publications

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“…Finally, if the pH value is too low to form nitrophenolates, the colourless H 2 ROH À species 8 may appear: Figure 3 (a) The absorption spectra of NPC in aqueous NaOH solution, pH 12: (1) immediately after preparation, k max = 398 nm; (2) after 5 min, (3) after 10 min, (4) after 30 min, (5) after 60 min, (6) after 90 min, (7) after 120 min, (8) after 150 min, (9) after 24 h, k max = 438 nm. (b) The absorption spectra of NPC in aqueous NaOH solution, pH 13: (1) immediately after preparation, k max = 392 nm; (2) after 2 min, (3) after 5 min, (4) after 7 min, (5) after 15 min, (6) after 30 min, (7) after 60 min, k max = 396; the final spectrum remains practically unchanged for several days…”

Section: Nitrophenol Crimson In Watermentioning

confidence: 99%

“…In CH 3 CN-H 2 O mixed buffer-free solvent, either of 1:9 or 9:1 volume ratio, the signals m/ z = 274.99 and 551.00 were registered in addition to those mentioned above. The first signal belongs to the dianion HROH 2À (7), while the second signal may be ascribed either to the monoanion H 2 ROH À (8) or to the associate R 2À (2) with the H 3 O + cation. Although during the electrospray experiments in water-acetonitrile solutions the dye exhibits two bands in the visible region ( Fig.…”

Section: Examining Nitrophenol Crimson Solutions By the Electrospray mentioning

confidence: 99%

“…Probably the sole exception is the communication by Nagase et al [6], but these authors did not provide spectral data. Meanwhile, the ionisation and tautomerism of tetranitrophenolphthalein and tetranitrofluorescein [7,8] have been described in detail.…”

Section: Introductionmentioning

confidence: 99%

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Revisiting tetranitrophenolsulfonephthalein

Mchedlov‐Petrossyan

Roshchyna

Shekhovtsov

et al. 2015

Coloration Technology

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Among the vast series of phenolsulfonephthalein dyes, the nitro derivatives and especially 3,3 0 ,5,5 0tetranitrophenolsulfonephthalein (nitrophenol crimson) remain practically unexplored, whereas the halogen and alkyl derivatives have been studied comprehensively. This striking difference is probably due to the enormous influence of the four NO 2 groups on the properties of the dye. As a result, the protolytic behaviour is unlike even that of tetrabromo phenolsulfonephthalein, and the recognised scheme of acid-base and tautomeric equilibrium of the sulfonephthaleins is unable to explain it. The molecular form H 2 R was isolated as a sultonic tautomer, and an X-ray crystal structure analysis was carried out. Our studies of the UV-vis absorption spectra in water, methanol, dimethyl sulfoxide, acetonitrile, acetone, and dichloromethane, as well as in aqueous micellar solutions of surfactants, allowed us to evaluate the true molar absorptivity of the dianion R 2À , and to elucidate the enormous tendency to form yellow trianionic carbinol ROH 3À , even in the presence of traces of H 2 O. Nuclear magnetic resonance and electrospray data confirm the proposed scheme of ionisation and tautomerism of nitrophenol crimson.

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Section: Nitrophenol Crimson In Watermentioning

confidence: 99%

Section: Examining Nitrophenol Crimson Solutions By the Electrospray mentioning

confidence: 99%

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Revisiting tetranitrophenolsulfonephthalein

Mchedlov‐Petrossyan

Roshchyna

Shekhovtsov

et al. 2015

Coloration Technology

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“…Previous studies published in 2000-2005 shed some light on the unusual properties of versatile nitrofluoresceins and nitrothiafluoresceins [3][4][5][6], in particular on the unusual behaviour of 2,4,5,7-tetranitrofluorescein (TNF) (X = Y = NO 2 ) [6]. It was assumed that in this case the formation of lactonic anions is possible, and for the TNF dianion R 2À , tautomer 5 is more preferred as compared with tautomer 6 (Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

“…The dianionic TNF lactone 5 is yellow, due to the absorption of the isolated nitrophenolate moieties [3,4,6]. This statement was confirmed by the appearance of an intense IR band atm = 1765 cm À1 (C=O stretching vibration of the lactone cycle) in dimethyl sulphoxide (DMSO) solutions after dissociation of the HR À monoanion into the R 2À dianion, upon the addition of alkali [6,7]. A similar band at m = 1790 cm À1 was registered for the neutral species H 2 R in the solid state.…”

Section: Introductionmentioning

confidence: 99%

The molecular structure of anionic species of 2,4,5,7‐tetranitrofluorescein as studied by electrospray ionisation, nuclear magnetic resonance and X‐ray techniques

Mchedlov‐Petrossyan

Steinbach

Vodolazkaya

et al. 2018

Coloration Technology

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Among the fluorescein dyes, the behaviour of their nitro derivatives in solution is most unusual, and yet at the same time rarely studied. In this study, their 13 C nuclear magnetic resonance and electrospray spectra are reported, which confirm, in concert with their ultraviolet-visible spectra, the molecular structures of the neutral and ionic species of 2,4,5,7-tetranitrofluorescein observed in different solvents and at various pH values. A peculiar property of this dye consists in its lactonisation of the double-charged anion, contrary to the wellknown coloured and fluorescent dianions of fluorescein, eosin, etc. Also, this dianion-lactone exhibits high ability for opening the pyran ring. This cleavage takes place at much lower pH values as compared with those for fluorescein and its halogen derivatives. The ruptured species can be formed as either lactone or carbinol; the latter appears as a result of the nucleophilic attack of a HO À on the central carbon atom. The corresponding molecular structures are identified via the electrospray method and X-ray analysis. The behaviour of some other nitrofluoresceins in alkaline media is also considered. Coloration TechnologySociety of Dyers and Colourists † Just now, an article "Syntheses of novel acid-base indicators by nitration of phenolphthalein and fluorescein" by Y. Negishi,

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Gas phase sensors for bases using rhodamine B in nafion films

Hwang

Levitsky

Euler

2010

J of Applied Polymer Sci

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A sensor and dosimeter specific to inorganic and organic amine bases composed of Rhodamine B dissolved in Nafion is prepared and evaluated. UV-vis, emission, and IR spectroscopies are used to monitor the presence of a variety of analytes, including aliphatic and aromatic amines. The Rhodamine B serves as a visual indicator of the presence of an analyte by turning from brown to pink upon exposure to aliphatic amines after sufficient exposure, thus acting as a visual monitor. The Rhodamine B also acts as a fluorescent sensor, which turns on upon exposure to the analyte. The sulfonic acid groups in the Nafion protonate the bases, giving unique signatures in the IR spectra allowing for differentiation of the bases.

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Fluorescent dye N,N′-dioctadecylrhodamine as a new interfacial acid–base indicator

Cited by 17 publications

References 20 publications

Revisiting tetranitrophenolsulfonephthalein

Revisiting tetranitrophenolsulfonephthalein

The molecular structure of anionic species of 2,4,5,7‐tetranitrofluorescein as studied by electrospray ionisation, nuclear magnetic resonance and X‐ray techniques

Gas phase sensors for bases using rhodamine B in nafion films

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